Jon Lester Contract Extension Should Be Bigger Priority for Red Sox Than Potential Pursuit of Masahiro Tanaka

Jon Lester, Masahiro TanakaThe Boston Red Sox should close the checkbook — unless they’re opening it for Jon Lester.

Masahiro Tanaka officially has hit the open market, and the bidding for the Japanese ace figures to be fierce. The New York Yankees, Los Angeles Dodgers and Chicago Cubs are among the big-market teams that could pursue Tanaka, and it’s believed the 25-year-old will receive a contract in excess of $100 million. But while the Red Sox have the financial flexibility to be aggressive in the Tanaka sweepstakes, Boston is better off shifting its attention toward Lester’s impending free agency.

Lester is slated to become a free agent next offseason. (He is coming off a five-year, $30 million extension that included a $13 million club option for 2014, which the Red Sox picked up shortly after their World Series victory.) The left-hander, who had a very good 2013 campaign, is in line for a big payday, which means this isn’t an ideal time for the Red Sox to ditch their disciplined free-agency approach, even if Tanaka represents an intriguing option.

General manager Ben Cherington has been reluctant to hand out expensive, long-term contracts to free agents, largely because the Red Sox have regretted such deals in the past. Boston now prefers to sign players to shorter deals, even if it means a higher average annual salary. Signing Lester likely will require that the Red Sox make an exception — similar to their exception for Dustin Pedroia, who received a seven-year, $100 million extension this past season — but locking up the proven southpaw to a long-term deal is a safer play than going all in on Tanaka, who never has thrown a pitch in Major League Baseball.

Tanaka could be the real deal. He went 24-0 with a 1.27 ERA for the Rakuten Golden Eagles of Japan’s Nippon Professional Baseball last season, and he owns a 99-35 record, 2.30 ERA and 1.11 WHIP in 175 career appearances (172 starts). Plus, at age 25 with just seven professional seasons under his belt, Tanaka is far from damaged goods despite the high pitch counts that often come with pitching in Japan. But while Tanaka is a worthwhile gamble for some big -league teams, the Red Sox, who currently have a surplus of starting pitching, don’t need to make a sizable financial commitment to an unknown commodity.

Perhaps signing Tanaka and re-upping Lester aren’t mutually exclusive, in which case a pursuit of Tanaka this offseason makes a little more sense for Boston than it otherwise would. It’s worth noting, however, that Clayton Kershaw and Max Scherzer are set to become free agents next offseason. There’s a chance that Kershaw and Scherzer will be extended by the Dodgers and Detroit Tigers, respectively, but if signing Lester and another high-priced starter is in Boston’s future, Tanaka isn’t the second hurler the Red Sox should eye.

Tanaka would be a luxury signing for the Red Sox this offseason. There’s no need for that when a more pressing issue and more appealing options are fast approaching.

Have a question for Ricky Doyle? Send it to him via Twitter at @TheRickyDoyle or send it here.

Masahiro Tanaka photo (right) via Facebook/Masahiro Tanaka

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